Copper-Catalyzed gamma-Selective and Stereospecific Allylic Cross-Coupling with Secondary Alkylboranes

Yasuda, Yuto; Nagao, Kazunori; Shido, Yoshinori; Mori, Seiji; Ohmiya, Hirohisa; Sawamura, Masaya

Copper-Catalyzed gamma-Selective and Stereospecific Allylic Cross-Coupling with Secondary Alkylboranes

"/Yasuda, Yuto/"Yasuda, Yuto , "/Nagao, Kazunori/"Nagao, Kazunori , "/Shido, Yoshinori/"Shido, Yoshinori , "/Mori, Seiji/"Mori, Seiji , "/Ohmiya, Hirohisa(1000040508876)/"Ohmiya, Hirohisa , "/Sawamura, Masaya(1000040202105)/"Sawamura, Masaya

Chemistry - A European Journal

21 ( 27 ) , pp.9666 - 9670 , 2015-06-26 , Wiley-Blackwell

ISSN:0947-65391521-3765

Description

The scope of the copper-catalyzed coupling reactions between organoboron compounds and allylic phosphates is expanded significantly by employing triphenylphosphine as a ligand for copper, allowing the use of secondary alkylboron compounds. The reaction proceeds with complete gamma-E-selectivity and preferential 1,3-syn stereoselectivity. The reaction of gamma-silicon-substituted allylic phosphates affords enantioenriched alpha-stereogenic allylsilanes.

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http://eprints.lib.hokudai.ac.jp/dspace/bitstream/2115/62278/1/CHEM_21_9666-.pdf

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Hokkaido University Collection of Scholarly and Academic Papers

Other information

subject	allylic substitution copper catalysis coupling secondary alkylborane stereoselectivity
publisher	Wiley-Blackwell
NIItype	Journal Article
format	application/pdf
language	eng
doi	info:doi/10.1002/chem.201501055
rights	This is the peer reviewed version of the following article: [Yuto Yasuda et al.,Copper-Catalyzed γ-Selective and Stereospecific Allylic Cross-Coupling with Secondary Alkylboranes. Chemistry - A European Journal, 21(27), p.9666–9670, 2015], which has been published in final form at [http://doi.org/10.1002/chem.201501055]. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.
textversion	author
NDC	430
URL	http://jairo.nii.ac.jp/0003/00050184/en

Copper-Catalyzed gamma-Selective and Stereospecific Allylic Cross-Coupling with Secondary AlkylboranesCopper-Catalyzed gamma-Selective and Stereospecific Allylic Cross-Coupling with Secondary Alkylboranes

Copper-Catalyzed gamma-Selective and Stereospecific Allylic Cross-Coupling with Secondary Alkylboranes